GtoPdb is requesting financial support from commercial users. Please see our sustainability page for more information.

besifloxacin   Click here for help

GtoPdb Ligand ID: 12877

Synonyms: Besivance® | BOL-303224-A | ISV-403 | SS734
Approved drug
besifloxacin is an approved drug (FDA (2009))
Compound class: Synthetic organic
Comment: Besifloxacin is a fluoroquinolone compound with broad-spectrum antibacterial activity against Gram-positive and Gram-negative pathogens [1-2].
2D Structure
Click here for help

2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

✖
Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 3
Topological polar surface area 86.87
Molecular weight 393.84
XLogP 3.11
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
Click here for help

SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

✖
Canonical SMILES C1CCN(C[C@@H](C1)N)C2=C(C3=C(C=C2F)C(=O)C(=CN3C4CC4)C(=O)O)Cl
Isomeric SMILES C1CCN(C[C@@H](C1)N)C2=C(C=C3C(=C2Cl)N(C=C(C3=O)C(=O)O)C4CC4)F
InChI InChI=1S/C19H21ClFN3O3/c20-15-16-12(18(25)13(19(26)27)9-24(16)11-4-5-11)7-14(21)17(15)23-6-2-1-3-10(22)8-23/h7,9-11H,1-6,8,22H2,(H,26,27)/t10-/m1/s1
InChI Key QFFGVLORLPOAEC-SNVBAGLBSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes. US FDA (2009)
IUPAC Name Click here for help
7-[(3R)-3-aminoazepan-1-yl]-8-chloro-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid
International Nonproprietary Names Click here for help
INN number INN
8958 besifloxacin
Synonyms Click here for help
Besivance® | BOL-303224-A | ISV-403 | SS734
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Besifloxacin
Other databases
CAS Registry No. 141388-76-3 (source: Scifinder)
ChEBI CHEBI:135622
ChEMBL Ligand CHEMBL1201760
DrugBank Ligand DB06771
DrugCentral Ligand 4111
GtoPdb PubChem SID 485205998
PubChem CID 10178705
Search Google for chemical match using the InChIKey QFFGVLORLPOAEC-SNVBAGLBSA-N
Search Google for chemicals with the same backbone QFFGVLORLPOAEC
Search PubMed clinical trials besifloxacin
Search PubMed titles besifloxacin
Search PubMed titles/abstracts besifloxacin
UniChem Compound Search for chemical match using the InChIKey QFFGVLORLPOAEC-SNVBAGLBSA-N
UniChem Connectivity Search for chemical match using the InChIKey QFFGVLORLPOAEC-SNVBAGLBSA-N
Wikipedia Besifloxacin